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Reaction of cholesterol 5,6-epoxides with simulated gastric juice

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Lipids

Abstract

Cholesterol 5α,6α-epoxide (α-epoxide) and cholesterol 5β,6β-epoxide (β-epoxide) were individually suspended in simulated gastric juice (pH 1.2) at 37 C, and their reaction was followed by gradient high performance liquid chromatography (HPLC) with flame ionization (FID) detection. Both epoxides reacted rapidly in the aqueous acid medium. The α-epoxide formed 6β-chlorocholestane-3β,5α-diol (α-chlorohydrin) and 5α-cholestane-3β,5,6β-triol (triol), while the β-epoxide formed 5α-chlorocholestane-3β,6β-diol (β-chlorohydrin) and triol. The isomeric chlorohydrins reacted further to form the triol. In mildly alkaline aqueous medium, each chlorohydrin reverted to the epoxide from which it was formed. The data suggest that both epoxides, which have been reported to have adverse health effects in animals, would be largely hydrolyzed in the stomach and to the triol, which also has been reported to have biological activity. The data furher suggest that residual chlorohydrins surviving stomach residence can be expected to revert to epoxide in the more alkaline intestinal environment.

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Abbreviations

α-Chlorohydrin:

6β-chlorocholestane-3β,5α-diol

α-epoxide:

cholesterol 5α,6α-epoxide

β-chlorohydrin:

5α-chlorocholestane-3β,6β-diol

β-epoxide:

cholesterol 5β,6β-epoxide

triol:

5α-cholestane-3β,5,6β-triol

FID:

flame ionization detector

GC:

gas chromatography

HPLC:

high performance liquid chromatography

TLC:

thin layer chromatography

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Authors and Affiliations

  1. Eastern Regional Research Center, U.S. Department of Agriculture, 600 East Mermaid Lane, 19118, Philadelphia, PA

    Gerhard Maerker, Edwin H. Nungesser & Frank J. Bunick

Authors
  1. Gerhard Maerker
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  2. Edwin H. Nungesser
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  3. Frank J. Bunick
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Maerker, G., Nungesser, E.H. & Bunick, F.J. Reaction of cholesterol 5,6-epoxides with simulated gastric juice. Lipids 23, 761–765 (1988). https://doi.org/10.1007/BF02536218

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  • DOI: https://doi.org/10.1007/BF02536218

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